$85 Find Cheap Flights from Chicago O'Hare Airport to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Caribbean Islands departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands.
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Flight Deals

Cheap Flights from O'Hare Intl to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$255
Santo Domingo
Santo Domingo1 stop$262
Montego Bay
Montego Bay1 stop$351
Oranjestad
Oranjestad1 stop$356
Nassau
Nassau1 stop$357
Kingston
Kingston2 stops$394
Simpson Bay
Simpson Bay1 stop$277
Providenciales
Providencialesnonstop$390
Port of Spain
Port of Spain1 stop$433
Bridgetown
Bridgetown1 stop$413
George Town
George Town1 stop$319
Willemstad
Willemstad1 stop$389
Castries
Castries3 stops$763
St. John's
St. John's1 stop$451
Puerto Plata
Puerto Plata1 stop$388
Aguadilla
Aguadilla1 stop$306
Punta Cana
Punta Cananonstop$255
Santo Domingo
Santo Domingo1 stop$262
Montego Bay
Montego Bay1 stop$351
Oranjestad
Oranjestad1 stop$356
Nassau
Nassau1 stop$357
Kingston
Kingston2 stops$394
Simpson Bay
Simpson Bay1 stop$277
Providenciales
Providencialesnonstop$390
Port of Spain
Port of Spain1 stop$433
Bridgetown
Bridgetown1 stop$413
George Town
George Town1 stop$319
Willemstad
Willemstad1 stop$389
Castries
Castries3 stops$763
St. John's
St. John's1 stop$451
Puerto Plata
Puerto Plata1 stop$388
Aguadilla
Aguadilla1 stop$306

Book Cheap O'Hare Intl to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Caribbean Islands

Sun, Jan 4 - Wed, Jan 14
Frontier Logo
5:05 am - 2:57 pmORD-SJU
7h 52m1 stop
Frontier Logo
9:37 pm - 2:29 pmSJU-ORD
18h 52m1 stop
$213Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
2:00 pm - 12:49 amORD-SJU
8h 49m1 stop
Multiple Airlines Logo
4:10 am - 1:58 pmSJU-ORD
11h 48m2 stops
$214Multiple Airlines
Find Deal
Thu, Jan 8 - Wed, Jan 14
Spirit Airlines Logo
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
$217Spirit Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Spirit Airlines Logo
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
$218Spirit Airlines
Find Deal
Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
7:30 pm - 10:48 amORD-SJU
13h 18m1 stop
American Airlines Logo
6:00 am - 9:35 amSJU-ORD
5h 35mnonstop
$221American Airlines
Find Deal
Tue, Jan 20 - Mon, Jan 26
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
2:05 am - 10:53 amSJU-ORD
10h 48m1 stop
$222United Airlines
Find Deal
Tue, Jan 20 - Tue, Jan 27
Delta Logo
1:55 pm - 11:59 pmORD-SJU
8h 04m1 stop
Delta Logo
3:55 pm - 11:57 pmSJU-ORD
10h 02m1 stop
$225Delta
Find Deal
Thu, Jan 29 - Mon, Feb 2
Delta Logo
10:24 am - 11:59 pmORD-SJU
11h 35m1 stop
Delta Logo
7:00 am - 5:45 pmSJU-ORD
12h 45m1 stop
$226Delta
Find Deal
Sun, Jan 18 - Thu, Jan 22
American Airlines Logo
3:15 pm - 9:54 pmORD-SJU
4h 39mnonstop
American Airlines Logo
4:28 pm - 8:00 pmSJU-ORD
5h 32mnonstop
$241American Airlines
Find Deal
Tue, Dec 2 - Fri, Dec 5
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
$268United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Caribbean Islands flights

Get data-powered insights and trends into flights from O'Hare Intl to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Chicago O'Hare Intl Airport found in the last 72 hours was to San Juan, at $219 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $219.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $421, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Caribbean Islands is January, when tickets cost $320 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $529 and $448 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Caribbean Islands?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago O'Hare Airport to Caribbean Islands, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$85
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago O'Hare Airport to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago O'Hare Airport to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $314 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $450.

Reviews of the top 5 airlines serving from O'Hare Intl to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8004 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.9Entertainment
7.3Food
Airline reviews

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

2.0 MediocreAnonymous, Nov 2025MOB - ATL
Read more Delta reviews

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Flight was delayed. (To be excepted because of TSA shortage) I’m super short and still struggled with leg room, there was no screen, and the seat didn’t recline at all.

The pilot would speak it was painfully load a d the crew had to know this! Maybe the were hesitant to tell him. It was just a mediocre experience and I was in Spirit first class!

My flight was cancelled last minute and I had to pay $1600 for flights, when my original flights were $300. It was a terrible experience.

Boarding was easy. I loved that they sat our family together even though we didn't pay for specific seats. I thought $5+ was a lot for pretzels and wish they had a small free snack.

The Hawaiian lady that boarded me was rude and the one help me a the ticket counter was rude

My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

The flight was cancelled at the last minute. Will never fly Spirit again. Without a doubt the worst airline around.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports